Literature DB >> 19710906

Tandem Chain Extension-Iodomethylation Reactions: Formation of alpha-Functionalized gamma-Keto Carbonyls.

Qinglin Pu1, Emerald Wilson, Charles K Zercher.   

Abstract

Sequential exposure of a zinc-organometallic intermediate, generated through a zinc carbenoid-mediated chain extension reaction of a beta-keto carbonyl, to trimethylsilylchloride and iodine provided regioselective formation of an alpha-iodomethyl-gamma-keto carbonyl. The iodomethyl functionality can be further manipulated to provide side chains that are potential mimics of alpha-amino acid side chains.

Entities:  

Year:  2008        PMID： 19710906      PMCID： PMC2598404          DOI： 10.1016/j.tet.2008.06.063

Source DB:  PubMed          Journal:  Tetrahedron        ISSN： 0040-4020            Impact factor:   2.457


  6 in total

1.  Formal synthesis of (+)-brefeldin A: application of a zinc-mediated ring expansion reaction.

Authors:  Weimin Lin; Charles K Zercher
Journal:  J Org Chem       Date:  2007-05-12       Impact factor: 4.354

2.  Tandem chain extension-homoenolate formation: the formation of alpha-methylated-gamma-keto esters.

Authors:  R Hilgenkamp; C K Zercher
Journal:  Org Lett       Date:  2001-09-20       Impact factor: 6.005

3.  Tandem chain extension-aldol reaction: syn selectivity with a zinc enolate.

Authors:  S Lai; C K Zercher; J P Jasinski; S N Reid; R J Staples
Journal:  Org Lett       Date:  2001-12-27       Impact factor: 6.005

4.  Stereocontrolled formation of ketomethylene isosteres through tandem chain extension reactions.

Authors:  Weimin Lin; Nancy Tryder; Fan Su; Charles K Zercher; Jerry P Jasinski; Ray J Butcher
Journal:  J Org Chem       Date:  2006-10-13       Impact factor: 4.354

5.  Ring expansions of beta-keto lactones with zinc carbenoids: syntheses of (+)-patulolide A and (+/-)-patulolide B.

Authors:  Matthew D Ronsheim; Charles K Zercher
Journal:  J Org Chem       Date:  2003-03-07       Impact factor: 4.354

6.  Zinc carbenoid-mediated chain extension: preparation of alpha,beta-unsaturated-gamma-keto esters and amides.

Authors:  Matthew D Ronsheim; Charles K Zercher
Journal:  J Org Chem       Date:  2003-05-30       Impact factor: 4.354
  6 in total
  2 in total

1.  A mechanistic investigation into the zinc carbenoid-mediated homologation reaction by DFT methods: is a classical donor-acceptor cyclopropane intermediate involved?

Authors:  Wilhelm A Eger; Charles K Zercher; Craig M Williams
Journal:  J Org Chem       Date:  2010-11-05       Impact factor: 4.354

2.  Stereoselective formation of a functionalized dipeptide isostere by zinc carbenoid-mediated chain extension.

Authors:  Weimin Lin; Cory R Theberge; Timothy J Henderson; Charles K Zercher; Jerry Jasinski; Ray J Butcher
Journal:  J Org Chem       Date:  2009-01-16       Impact factor: 4.354
  2 in total

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